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  • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
  • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
  • H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
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  • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S428/00—Stock material or miscellaneous articles
  • Y10S428/917—Electroluminescent

Definitions

• the present invention relates to a layer assembly for electro-optic devices containing an electrophosphorescent material and to electroluminescent devices comprising this layer assembly.
• Electroluminescent arrangements are versatile, for example in the manufacture of screens or displays. Recently, the interest in emissive displays and display devices, especially taking advantage of the electrophosphorescence to increase the luminous efficacy ( s. Baldo et al., Appl. Phys. Lett., Vol 75, No 1, 4, 1999 ; WO 00/70 655 A2 ).
• Triplet-based emission of light is known by the term phosphorescence ( WO 00/70 655 A2 ).
• the advantage of phosphorescence over fluorescence is that the majority of triplet-based excitons formed by recombination of holes and electrons in an electroluminescent layer are available for luminescent energy transfer.
• a coordinated layer structure of the electroluminescent arrangement is necessary.
• a hole injection layer is applied to a substrate coated with indium-tin-oxide (ITO) by a vacuum process, ie, vapor deposition of a low molecular weight amine.
• ITO indium-tin-oxide
• a vacuum process ie, vapor deposition of a low molecular weight amine.
• the inherent roughness of the ITO surface on the substrate is inevitably displayed and maintained.
• roughnesses have a very negative effect on the operation of an electroluminescent device since they lead to voltage peaks which result in faster aging and degradation of the layer structure.
• OLEDs organic light-emitting diodes having a hole conductor layer and an electron transport layer.
• These layers contain compounds, for example tris (8-hydroxyquinoline) aluminum (Alq 3 ), which can be applied only by a complex and expensive vapor deposition process. It would be desirable to have much simpler and more established processing from solution using spin coating, casting or ink-jet methods.
• OLEDs For the production of OLEDs are according to WO 00/70 655 A2 used as transparent substrates polymer films such as polycarbonate or other transparent polymers. These substrates are provided with a conductive layer, preferably indium tin oxide (ITO).
• ITO indium tin oxide
• the disadvantage is the excessive roughness of the conductive layer, which can lead to short circuits during operation and high rejection during production.
• conventional inorganic conductive layers on plastic substrates always have greater roughness than on glass.
• ITO-PET polyethylene terephthalate
• the object of the invention was therefore the development of new layer arrangements, the. Allow emission of light from excited triplet states and do not show the disadvantages mentioned.
• a layer of an organic conductive polymer system is applied directly to the already existing conductive layer, eg ITO, of the substrate.
• the conductive polymer system surface roughnesses of the conductive layer on the substrate, especially on plastic substrates, are balanced.
• the polymer system spans any existing Cracks. It ensures by its ductility and toughness that, even after handling the layer system according to the invention, any existing cracks remain overstretched with conductive paths and the surface conductivity is not interrupted.
• the invention relates to a layer arrangement comprising at least one transparent substrate containing an electrically conductive layer, an electro-optically active layer, and another substrate containing an electrically conductive layer, wherein at least one of the two electrically conductive substrates additionally coated with an organic conductive polymer system and the electro-optically active layer contains an electrophosphorescent compound.
• the layer arrangement according to the invention permits light emission in the form of phosphorescence and prevents short circuits in the operation of OLEDs containing this layer arrangement by using an electrically conductive polymer system on a transparent conductive inorganic layer (TCO layer) on a substrate.
• TCO layer transparent conductive inorganic layer
• electro-optically active layer a layer containing an electro-optic compound, i. a compound that emits light when recombined by electrons and holes.
• electrophosphorescent compounds are compounds which emit light under the phenomenon of phosphorescence during the radiative recombination of electrons and holes. These compounds also show the appearance of photoluminescence in the form of phosphorescence upon excitation with light. In contrast to fluorescence, the excitation states that lead to phosphorescence show a longer lifetime.
• the quantum efficiency of fluorescence is theoretically limited by the spin statistics (25% singlet states leading to fluorescence, in contrast to 75% triplet states). In the case of phosphorescent materials, on the other hand, all excited states can radiantly decay, which manifests itself in a higher quantum yield.
• the electrically conductive layer of the transparent substrate is a transparent conductive inorganic layer, the organic conductive polymer system being applied to this layer.
• a layer of indium tin oxide is used as the transparent inorganic conductive layer.
• Suitable electrophosphorescent compounds are made WO 00/70 655 A2 known.
• phosphorescent organic iridium or osmium compounds can be used.
• Unsubstituted fac-tris (2-phenylpyridine) iridium of the formula (I) is particularly preferably used as the electrophosphorescent compound.
• substituents are (C 1 -C 8 ) -alkyl, halogen, cyano (CN) and CF 3 , where both the phenyl ring and the pyridine ring of the phenylpyridine ligands can carry one or more identical or different substituents and each Phenylpyridine ligand is preferably identically substituted.
• the substituents are preferably (C 1 -C 6 ) -alkyl, F or CF 3 , particularly preferably F or CF 3 .
• electrophosphorescent compound it is also possible to use iridium complexes of the general formula (II) be used, where R x and R y independently of one another are optionally substituted (C 1 -C 8 ) -alkyl, optionally substituted (C 6 -C 10 ) -aryl or halogen-substituted (C 6 -C 10 ) -aryl.
• R x and R y independently of one another are (C 1 -C 6 ) -alkyl, phenyl or fluorine-substituted phenyl, in particular (C 1 -C 6 ) -alkyl or phenyl.
• electrophosphorescent compound furthermore, iridium complexes of the general formula (III) suitable, wherein R v and R w together form an aromatic, sulfur-containing heterocycle having 5 or 6 ring atoms, it being possible for further aromatic rings, preferably C 6 rings, to be condensed onto this heterocycle.
• R v and R w together form a thiophene ring.
• iridium complexes of the general formula (IV) are used, which differ from the compounds of formula (I) by replacing a phenylpyridine ligand by a pyridine-2-carboxylic acid ligand.
• Phenylpyridine ligands and pyridine-2-carboxylic acid ligand may optionally be substituted.
• suitable substituents are (C 1 -C 8 ) -alkyl, halogen, cyano (CN) and CF 3 , where both the phenyl ring and the pyridine ring of the phenylpyridine ligands and the pyridine ring of the pyridine-2-carboxylic acid ligand may carry one or more identical or different substituents and each phenylpyridine ligand is preferably identically substituted.
• the substituents are preferably (C 1 -C 6 ) -alkyl, F or CF 3 , particularly preferably F or CF 3 .
• the listed iridium complexes of the formulas (I) to (IV) can be prepared in a known manner from suitable iridium compound, preferably iridium (III) acetylacetonate, by ligand exchange.
• ligands are commercially available or can be prepared by conventional methods.
• the organic conductive polymer system may be e.g. to act a system based on polyanilines, polypyrroles or polythiophenes.
• the conductive polymer system is understood to mean a system which, in addition to the actual organic conductive polymer, may contain further constituents. These may be, for example, film formers, crosslinkers, thermosolvents, binders or electrical conductivity-improving additives. Examples are in US Pat. No. 5,766,515 or EP-A 602 713 described.
• R 3 , R 4 independently of one another represent hydrogen, but not both at the same time, or one of the abovementioned radicals, the radical being substituted by a sulfonate group.
• R 5 is preferably one of the abovementioned radicals, the radical being substituted by a sulfonate group.
• n in the abovementioned formulas is an integer from 4 to 15.
• polyanions used are the anions of polymeric carboxylic acids, such as polyacrylic acids, polymethacrylic acids, polymaleic acids and polymeric sulfonic acids, such as polystyrenesulfonic acids and polyvinylsulfonic acids.
• polymeric carboxylic acids such as polyacrylic acids, polymethacrylic acids, polymaleic acids and polymeric sulfonic acids, such as polystyrenesulfonic acids and polyvinylsulfonic acids.
• These polycarboxylic and sulfonic acids may also be copolymers of vinyl carboxylic and vinyl sulfonic acids with other polymerizable monomers such as acrylic acid esters and styrene.
• PSS polystyrene sulfonic acid
• the molecular weight of the polyanionic polyacids is preferably 1,000 to 2,000,000, more preferably 2,000 to 500,000.
• the polyacids or their alkali salts are commercially available, e.g. Polystyrenesulphonic acids and polyacrylic acids, or else can be prepared by known processes (see, for example, Houben Weyl, Methoden der organischen Chemie, Vol. E 20 Macromolecular Substances, Part 2, (1987), p. 1141 and following).
• the polyalkylenedioxythiophenes carry positive and negative charges in the structural unit.
• the polyalkylenedioxythiophenes are prepared by oxidative polymerization. As a result, they receive positive charges, which are not shown in the formulas, since their number and their position can not be determined correctly.
• the polythiophene dispersion can be applied to the transparent conductive substrate by well-established low-cost methods such as casting, printing, spraying, dipping, flooding or inkjet. There is no costly vacuum process necessary.
• a hole conductor layer containing aromatic amine is applied to the electrically conductive polymer system.
• a compilation of possible amines is in EP-A 0 532 798 given.
• R 7 and R 8 are more preferably independently of one another unsubstituted phenyl or naphthyl or phenyl or naphthyl which is in each case monosubstituted to trisubstituted by methyl, ethyl, n-, iso-propyl, methoxy, ethoxy, n- and / or isopropoxy.
• R 6 is preferably hydrogen, (C 1 -C 6 ) -alkyl, such as, for example, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, or chlorine.
• further hole conductors e.g. in the form of a mixture with the tertiary amino compound, be used to construct the electroluminescent element.
• it may be one or more compounds of the formula (VI), which also includes mixtures of isomers, on the other hand also mixtures of hole-transporting compounds with tertiary amino compounds - with the general formula (VI) - with different structure.
• the compounds can be used in any ratio.
• Examples include:
• Materials which have hole-conducting properties and can be used in pure form or as a mixing partner to the tertiary amino compounds are for example, the following compounds wherein X 1 to X 4 are independently H, halogen, alkyl, aryl, alkoxy, aryloxy.
• the layer arrangement according to the invention preferably additionally comprises an electron transport layer.
• an electron transport layer A variety of compounds suitable for use in such a layer are already known.
• a gallium complex from the group Ga (qa) 2 OR 9 , Ga (qa) 2 OCOR 9 or Ga (qa) 2 -O-Ga (qa) 2 is used to produce the electron transport layer, wherein R 9 is substituted or unsubstituted alkyl, aryl, arylalkyl or cycloalkyl and stands.
• these gallium compounds can be processed both from solution and by vapor deposition.
• Suitable solvents are, for example, methanol, ethanol, n-propanol or isopropanol.
• R 9 preferably represents halogen-substituted or cyano-substituted or unsubstituted, optionally branched alkyl, in particular halogen-substituted or cyano-substituted or unsubstituted, optionally branched (C 1 -C 8 ) -alkyl, particularly preferably substituted by halogen or cyano or unsubstituted, optionally branched (C 1 -C 6 ) -alkyl.
• halogen fluorine and chlorine are preferable.
• the layer arrangement according to the invention between the electro-optically active layer and the electron transport layer contains a barrier layer.
• the barrier layer contains bathocuproin (X).
• glass As a transparent substrate provided with a conductive layer, glass, thin glass (flexible glass) or plastics are suitable.
• plastics are: polycarbonates, polyesters, copolycarbonates, polysulfone, polyethersulfone, polyimide, polyethylene, polypropylene or cyclic polyolefins or cyclic olefin copolymers (COC), hydrogenated styrene polymers or hydrogenated styrene copolymers.
• Preferred polymers are polycarbonates, polyesters, polysulfone, polyethersulfone, cyclic olefin copolymers, hydrogenated styrenic polymers and hydrogenated styrenic copolymers. From the group of the polyesters PET and PEN (polyethylene terephthalate or polyethylene naphthenate) are preferred.
• Suitable polymer substrates are, for example, polyester films, PES films from Sumitomo or polycarbonate films from Bayer AG (Makrofol®).
• These substrates may be scratch-resistant and / or chemical-resistant by an additional layer, e.g. Marnot® films (Bayer AG).
• an additional layer e.g. Marnot® films (Bayer AG).
• Polycarbonates or copolycarbonates containing one of the following segments are particularly suitable from the group of polycarbonates:
• the layer arrangement according to the invention can be encapsulated.
• the layer arrangement according to the invention is suitable in particular as an electroluminescent device. Accordingly, electroluminescent devices which comprise a layer arrangement according to the invention are likewise provided by the invention.
• the layer arrangement according to the invention can be produced, for example, as follows: An organic electrically conductive polymer is applied in the form of a solution or dispersion to a substrate which is coated in an electrically conductive manner with an indium-tin-oxide layer (ITO layer). A subsequent annealing process serves to remove the solvent components. The preferably used amines of the formula (VI) are then likewise applied to the layer of the organic conductive polymer system in the form of a wet coating step. Again, an annealing step to remove the solvent. A subsequent electro-optically active layer, and optionally a barrier layer are applied by a vapor deposition process.
• ITO layer indium-tin-oxide layer
• a now following electron transport layer of a gallium complex compound is then preferably again applied from a solution, for example in methanol, to the electro-optically active layer or the barrier layer.
• a solution for example in methanol
• Table 1 shows the influence of Baytron ® P-solution on the surface of the substrate. ⁇ b> ⁇ u> Table 1 ⁇ / u> ⁇ /b> substratum Roughness r a (nm) a) Glass / ITO 2.5 b) Glass / ITOBaytron ® P 1.6 c) Polyester (PET) / ITO 3.9 d) Polyester (PET) / ITOBaytron ® P 2.5
• the roughnesses were determined by atomic force microscopy (AFM).
• the pattern d) has no visible surface cracks even after repeated mechanical treatment - bending, rolling, etc.
• the Baytron ® P-coated substrates can, for construction of electro-optically active devices, such as Elektrophosphoreszenzan builden be used.

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